The reactions of some 2-pyridylthioesters with imines in the presence of AlBr3 or EtAlCl2 and of a tertiary amine afford β-lactams in a simple one-pot procedure with fair to high trans stereoselectivity. The condensation can be also carried out in the absence of base and with sub-stoicheiometric amounts of the Lewis acid. The possible mechanisms of the process are discussed.
Stereoselective one-pot synthesis of β-lactams by reaction of 2-pyridylthioesters with imines in the presence of AlBr3 or EtAlCl2 / R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, O. Martini, V. Molteni. - In: TETRAHEDRON. - ISSN 0040-4020. - 52:7(1996), pp. 2583-2590.
Stereoselective one-pot synthesis of β-lactams by reaction of 2-pyridylthioesters with imines in the presence of AlBr3 or EtAlCl2
R. AnnunziataPrimo
;M. BenagliaSecondo
;M. Cinquini;F. Cozzi;
1996
Abstract
The reactions of some 2-pyridylthioesters with imines in the presence of AlBr3 or EtAlCl2 and of a tertiary amine afford β-lactams in a simple one-pot procedure with fair to high trans stereoselectivity. The condensation can be also carried out in the absence of base and with sub-stoicheiometric amounts of the Lewis acid. The possible mechanisms of the process are discussed.
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